A SYNTHETIC APPROACH TO DERIVE EXO-GLUCAL DERIVATIVES THROUGH THE REACTION OF A 1-C-VINYLATED GLUCOPYRANOSE DERIVATIVE WITH PHENOLS

In this study, a synthetic approach to prepare exo-glucal derivatives through the reaction of a 1-C-vinylated glucopyranose derivative with phenols in the presence of an appropriate promoter has been investigated. The reaction between 2,3,4,6-tetra-O-benzyl-1-C-vinyl-alpha-D-glucopyranose and different phenols using 5 mol% Bi(OTf)(3) produced the corresponding exo-glucal derivatives as major products along with spiro O-glucoside derivatives as minor products.